DE2331398B2 - Esters of 3-phenyl-4-hydroxy-6-halopyridazine compounds, their preparation and herbicidal compositions containing them - Google Patents

Esters of 3-phenyl-4-hydroxy-6-halopyridazine compounds, their preparation and herbicidal compositions containing them

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Publication number
DE2331398B2
DE2331398B2 DE2331398A DE2331398A DE2331398B2 DE 2331398 B2 DE2331398 B2 DE 2331398B2 DE 2331398 A DE2331398 A DE 2331398A DE 2331398 A DE2331398 A DE 2331398A DE 2331398 B2 DE2331398 B2 DE 2331398B2
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Germany
Prior art keywords
found
phenyl
calc
compounds
pyridazinyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
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DE2331398A
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German (de)
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DE2331398A1 (en
DE2331398C3 (en
Inventor
Engelbert Ing Auer
Alfred Dr Diskus
Engelbert Ing Kloimstein
Hubert Dr Mayr
Rupert Dr Schoenbeck
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Agrolinz Agrarchemikalien Muenchen 8000 Muen GmbH
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Lentia GmbH
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Application filed by Lentia GmbH filed Critical Lentia GmbH
Priority to DE2331398A priority Critical patent/DE2331398C3/en
Priority to AT566173A priority patent/AT326137B/en
Priority to AT566273A priority patent/AT326409B/en
Priority to AR254304A priority patent/AR205890A1/en
Priority to CS3798A priority patent/CS172993B2/cs
Priority to YU1553/74A priority patent/YU39604B/en
Priority to HU74CE1003A priority patent/HU173167B/en
Priority to GB2550574A priority patent/GB1441056A/en
Priority to FR7419919A priority patent/FR2234296B1/fr
Priority to DK312374A priority patent/DK137724C/en
Priority to CA202,269A priority patent/CA1013745A/en
Priority to ZA00743763A priority patent/ZA743763B/en
Priority to CH819074A priority patent/CH585013A5/xx
Priority to IL45037A priority patent/IL45037A/en
Priority to BR4941/74A priority patent/BR7404941D0/en
Priority to IT68890/74A priority patent/IT1050518B/en
Priority to US05/480,309 priority patent/US3953445A/en
Priority to LU70352A priority patent/LU70352A1/xx
Priority to AU70181/74A priority patent/AU484628B2/en
Priority to DD179248A priority patent/DD112205A1/xx
Priority to BE145633A priority patent/BE816574A/en
Priority to JP6976774A priority patent/JPS5420574B2/ja
Priority to PL1974172058A priority patent/PL100063B1/en
Priority to SU2037601A priority patent/SU514569A3/en
Priority to NL747408275A priority patent/NL154213B/en
Priority to PL1974193123A priority patent/PL98549B1/en
Priority to SU2117535A priority patent/SU526274A3/en
Publication of DE2331398A1 publication Critical patent/DE2331398A1/en
Priority to KE2673A priority patent/KE2673A/en
Publication of DE2331398B2 publication Critical patent/DE2331398B2/en
Application granted granted Critical
Publication of DE2331398C3 publication Critical patent/DE2331398C3/en
Expired legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D237/14—Oxygen atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

in der Hai ein Chlor- oder Bromatom, R einen geradkettigen oder verzweigten Alkylrest mit 1 bis 12 C-Atomen, X ein Sauerstoffatom und Y ein Schwefelatom, oder umgekehrt, bedeutet.in Hai a chlorine or bromine atom, R a straight chain or branched alkyl radical with 1 to 12 carbon atoms, X an oxygen atom and Y a sulfur atom, or vice versa, means.

2. 0-[3-Phenyl-6-chlor-pyridazinyl-(4)]-S-(n-pro-2. 0- [3-phenyl-6-chloro-pyridazinyl- (4)] - S- (n-pro-

pyl)-thiocarbonatpyl) thiocarbonate

3. O-[3-Phenyl-6-chlor-pyridazinyl-(4)]-S-(n-bu-3. O- [3-phenyl-6-chloro-pyridazinyl- (4)] - S- (n-bu-

tyl)-thiocarbonattyl) thiocarbonate

4. O-[3- Phenyl-6-brom-pyridazinyl-(4)]-S-(n-butyl)-thiocarbonat 4. O- [3-phenyl-6-bromo-pyridazinyl- (4)] - S- (n-butyl) thiocarbonate

5. O-[3-Phenyl-6-chlor-pyridazinyl-(4)]-S-[butyl-(2)]-thiocarbonat 5. O- [3-phenyl-6-chloro-pyridazinyl- (4)] - S- [butyl- (2)] thiocarbonate

6. O-[3-Phenyl-6-chlor-pyridazi:iyI-(4)]-S-(n-pentyl)-thiocarbonat 6. O- [3-phenyl-6-chloropyridazi: iyI- (4)] - S- (n-pentyl) thiocarbonate

7. O-[3-Phenyl-6-chlor-pyridazinyl-(4)]-S-[3-methyl-butyl-( I )]-thiocarbonat7. O- [3-phenyl-6-chloro-pyridazinyl- (4)] - S- [3-methyl-butyl- ( I)] - thiocarbonate

8. O-[3-PhenyI-6-chIor-pyridazinyl-(4)]-S-(n-hexyl)-thiocarbonat 8. O- [3-Phenyl-6-chloro-pyridazinyl- (4)] - S- (n-hexyl) thiocarbonate

9. O-[3- PhenyI-6-chlor-pyridazinyl-(4)]-S-(n-heptyl)-thiocarbonat 9. O- [3-Phenyl-6-chloro-pyridazinyl- (4)] - S- (n-heptyl) thiocarbonate

10. O-[3-Phenyl-6-chlor-pyridazinyl-(4)]-S-(n-octyl)-thiocarbonat 10. O- [3-Phenyl-6-chloro-pyridazinyl- (4)] - S- (n-octyl) thiocarbonate

11. O-[3-Phenyl-6-chlor-pyridazinyl-(4)]-O-(äthyl)-thionocarbonat 11. O- [3-Phenyl-6-chloro-pyridazinyl- (4)] - O- (ethyl) thionocarbonate

12. O-[3-Phenyl-6-chlor-pyridazinyl-(4)]-O-(n-propyl)-thionocarbonat 12. O- [3-Phenyl-6-chloro-pyridazinyl- (4)] - O- (n-propyl) thionocarbonate

13. O-[3-Phenyl-6-chlor-pyridazinyl-(4)]-O-(n-buiyl)-thionocarbonat 13. O- [3-Phenyl-6-chloro-pyridazinyl- (4)] - O- (n-butyl) thionocarbonate

14. O-[3-Phenyl-6-chlor-pyridazinyl-(4)]-O-(isobuiyl)-thionocarbonat 14. O- [3-Phenyl-6-chloro-pyridazinyl- (4)] - O- (isobuiyl) thionocarbonate

15. O-[3-Phenyl-6-chlor-pyridazinyl-(4)]-O-(n-hexyl)-thionocarbonat 15. O- [3-Phenyl-6-chloro-pyridazinyl- (4)] - O- (n-hexyl) thionocarbonate

16. Verfahren zur Herstellung von Estern von 3-Phenyl-4-hydroxy-6-halogen-pyridazinverbindungen nach den Ansprüchen I bis 17, dadurch gekennzeichnet, daß S-Phenyl-o-chloM-hydroxy-pyridazin oder 3-Phenyl-6-brom-4-hydroxy-pyridazin oder deren Salze gegebenenfalls in Anwesenheit eines Lösungsmittels und gegebenenfalls unter Zusatz eines Säureacceptors mit einem Säurechlorid der allgemeinen Formel16. Process for the preparation of esters of 3-phenyl-4-hydroxy-6-halo-pyridazine compounds according to claims I to 17, characterized in that that S-phenyl-o-chloM-hydroxypyridazine or 3-phenyl-6-bromo-4-hydroxypyridazine or salts thereof, optionally in the presence of a solvent and optionally with the addition of an acid acceptor with an acid chloride of the general type formula

ClCl

Y RY R

in der X. Y und R wie in Formel I definiert sind, in an sich bekannter Weise umgesetzt werden,in which X, Y and R are as defined in formula I, are reacted in a manner known per se,

17. Herbizides Mittel zur selektiven Bekämpfung von Unkräutern in Kultiirpflanzungen, dadurch gekennzeichnet, daß es als Wirkstoff eine oder mehrere Verbindungen gemäß Anspruch 1 — 15 sowie Streck- oder Verdünnungsmittel und/oder Netzmittel enthält.17. Herbicidal agent for the selective control of weeds in cultivated plants, characterized in that that there is one or more compounds according to claims 1-15 as the active ingredient Contains extenders or thinners and / or wetting agents.

Die Erfindung betrifft den in den Ansprüchen gekennzeichneten Gegenstand.The invention relates to the subject matter characterized in the claims.

Es ist schon seit längerer Zeit bekannt, daß Pyridazinderivate das Pflanzenwachstum beeinflussen. So sind Pyridazine, die zwei oder drei Halogenatome oder bis zu zwei Halogenatome und außerdem alkylierte Aminogruppen, Alkoxygruppen oder Alkylmerkaptogruppen enthalten, in der AT-PS 1 98 997 als Mittel zur Beeinflussung des Pflanzenwachstums beschrieben. Die dort im Detail beschriebenen Verbindungen sind entweder Totalherbizide oder bewirken anderweitige Beeinflussungen der Pflanze, wie etwa Blattabfall.It has been known for a long time that pyridazine derivatives affect plant growth. So are pyridazines that have two or three halogen atoms or up to two halogen atoms and also alkylated amino groups, alkoxy groups or alkyl mercapto groups contained, described in AT-PS 1 98 997 as a means for influencing plant growth. the The compounds described in detail there are either total herbicides or have other effects of the plant, such as leaf waste.

Ferner ist die 3-Chlorpyridazin-6-oxyessigsäure als hormonen wirkendes Unkrautbekämpfungsmittel geeignet, das jedoch über keine ausreichende Breitenwirkung verfügtFurthermore, 3-chloropyridazine-6-oxyacetic acid is suitable as a hormone-acting weed control agent, However, this does not have a sufficient broad impact

In der DE-OS 15 67 131 und DE-OS 19 tf< *20 sind schließlich Phenylpyridazinäther beschrieben, die zur Bekämpfung von Gräsern in Reiskulturen dienen können. In DE-OS 15 67 131 and DE-OS 19 tf < * 20 Finally, phenylpyridazine ethers are described, which can be used to control grasses in rice crops.

Es konnte nun gefunden werden, daß die erfindungsgemäßen Verbindungen sehr günstige herbizide Eigenschaften aufweisen und außerdem für viele Nutzpflanzen, z. B. Getreide, gute Verträglichkeit zeigen.It has now been found that the compounds according to the invention have very favorable herbicidal properties have and also for many useful plants, e.g. B. cereals, show good tolerance.

Innerhalb der zu den Gräsern zählenden Pflanzen sind allerdings erhebliche Unterschiede hinsichtlich der Pflanzenverträglichkeit gegeben. Während die Getreidearten Mais und Reis bei Aufwandmengen, die für eine Abtötung der Unkräuter ausreichen, sich gegenüber den erfindungsgemäßen Verbindungen als tolerant erweisen, zählen die Vertreter der Unkrauthirsen (Echinochloa crus galli = Hühnerhirse, Setaria viridis = Grüne Borstenhirse, Digitaria filiformis = Fadenfingerhirse) zu den empfindlichen Gramineen, so daß eine selektive Bekämpfung dieser Schadgräser mit den erfindungsgemäßen Verbindungen möglich ist. Der Bekämpfungserfolg ist bei Anwendung der Verbindungen im Jugendstadium der Pflanzenentwicklung (2- bis 4-Blattstadium der Unkrauthirsen) am besten.Within the grass plants, however, there are considerable differences with regard to the Plant tolerance given. While the grain types maize and rice at application rates that are suitable for killing the weeds is sufficient to be tolerant of the compounds according to the invention prove to include the representatives of the weed millet (Echinochloa crus galli = barn millet, Setaria viridis = Green millet, Digitaria filiformis = thread millet) to the sensitive gramineae, so that selective control of these grass weeds is possible with the compounds according to the invention. The control success is when using the compounds in the youth stage of plant development (2 to 4 leaf stage the weed millet) is best.

Bei den erfindungsgemäßen Verfahren zur Herstellung der neuen Ester von 3-Phenyl-4-hydroxy-6-halogen-pyridazinverbindungen der allgemeinen Formel I können organische Lösungsmittel, insbesondere inerte aromatische Kohlenwasserstoffe, eingesetzt werden.In the process according to the invention for the preparation of the new esters of 3-phenyl-4-hydroxy-6-halo-pyridazine compounds of the general formula I, organic solvents, in particular inert aromatic hydrocarbons, can be used.

Es ist vorzugsweise möglich, für diese Reaktionen die Salze der in Anspruch 16 genannten Hydroxypyridazine mit tertiären Aminen einzusetzen, wobei sich im wesentlichen ein zusätzlicher Säureacceptor erübrigt. Diese Reaktionen spielen sich meist br normaler oder leicht erhöhter Temperatur ab, jedoch sind auch höhere Temperaturen nicht ausgeschlossen.It is preferably possible to use the salts of the hydroxypyridazines mentioned in claim 16 for these reactions to be used with tertiary amines, an additional acid acceptor being essentially unnecessary. These reactions usually play out br normal or slightly increased temperature, but higher temperatures are also not excluded.

Im allgemeinen ist es vorteilhaft, die Umsetzung in Abwesenheit von Hydroxylgruppen enthaltenden Verbindungen, wie Alkohole oder Wasser, auszuführen.In general, it is advantageous to carry out the reaction in the absence of compounds containing hydroxyl groups, such as alcohols or water.

Die gewonnenen erfindungsgemäßen Verbindungen stellen meist Flüssigkeiten oder Feststoffe mit niedrigem Schmelzpunkt dar. Das als Ausgangsmaterial verwendete 3-Phenyl-4-hydroxy-6-chlorpyridazin mit dem Fp. 22O0C (Zersetzung) kann aus 3-Phenyl-4,6-dichlorpyridazin durch Erhitzen mit Natronlauge erhalten werden. The obtained compounds of the invention usually represent liquids or solids with low melting point. The used as starting material 3-phenyl-4-hydroxy-6-chloropyridazine of mp. 22O 0 C (decomposition) may be made of 3-phenyl-4,6-dichloropyridazine can be obtained by heating with sodium hydroxide solution.

Ebenso ist das 3-Phenyl-4-hydroxy-6-brompyridazin, Fp. 215"C (Zersetzung), durch Umsetzung von 3-Phenyl-4,6-dibrompyridazin mit Natronlauge in der Siedehitze zugänglich.3-Phenyl-4-hydroxy-6-bromopyridazine, m.p. accessible with sodium hydroxide solution at the boiling point.

Die erfindungsgemäßen Ester der allgemeinen Formel I sind meist viskose Flüssigkeiten mit hohem Siedepunkt, die nicht unzersetzt destillierbar sind.The esters of the general formula I according to the invention are mostly viscous liquids with a high boiling point, which cannot be distilled without decomposition.

Die erfindiingsgemäßen Mittel können in Form von Dispersionen, Emulsionen, als staubförmige Zubereitung oder in Form von Granulaten vorliegen.The agents according to the invention can be in the form of Dispersions, emulsions, as powdery preparations or in the form of granules.

Für Mittel in Form wäßriger Dispersionen oder Emulsionen empfiehlt sich der Zusatz eines Dispersionsmittels, tu B. Natriumoleyl-methyl-taurid. Als feste Streckmittel kommen u. a. verschiedene Tonsorten, z. B. Kaolin, in BetrachtFor compositions in the form of aqueous dispersions or emulsions, the addition of a dispersing agent, tu B. Natriumoleyl-methyl-tauride is recommended. As solid extenders, there are various types of clay, e.g. B. kaolin into consideration

Vorteilhaft ist bei den erfindungsgemäßen Verbindungen die Kombination mit einem nicht phytotoxischen öl, z. B. einem Mineralöl-Emulgator-Gemisch, bestehend aus einem paraffinischen Mineralöl und einem Emulgator. Durch Zusatz eines solchen »Spray-Oils« zu einer Spritzlösung der erfindungsgemäßen Verbindungen kann die herbizide Wirkung noch gesteigert werden. Solche Kombinationen enthalten üblicherweise 0,1 bis 10 kg der erfindungsgemäßen Verbindung und 1 bis 10 Liter eines nicht phytotoxischen Öles, verteilt in einer Menge von 50 bis 1000 Liter Wasser.In the case of the compounds according to the invention, the combination with a non-phytotoxic one is advantageous oil, e.g. B. a mineral oil-emulsifier mixture, consisting of a paraffinic mineral oil and an emulsifier. By adding such a »spray oil« the herbicidal action can be increased still further with a spray solution of the compounds according to the invention will. Such combinations usually contain 0.1 to 10 kg of the compound according to the invention and 1 to 10 liters of a non-phytotoxic oil, distributed in an amount of 50 to 1000 liters of water.

Da diese Verbuidungen nicht im Sinne von Wuchsstoffen wirksam sind, ist die Gefahr einer Schädigung von Nachbarkulturen wesentlich verringert. Sie eignen sich daher auch bevorzugt zur Unkrautbekämpfung in Kulturpflanzungen in unmittelbarer Nähe wuchsstoffempfindlicher Kulturen.Since these compounds are not in the sense of growth substances are effective, the risk of damage to neighboring crops is significantly reduced. You own therefore also preferred for weed control in crops in the immediate vicinity more sensitive to growth substances Cultures.

Die Toxizitätswerte liegen günstig. So besitzt die Verbindung 0-[3-Phenyl-6-chlorpyridazinyl-(4)]-S-(noctylj-thiocarbonat folgende akute orale LD50:The toxicity values are favorable. The compound has 0- [3-phenyl-6-chloropyridazinyl- (4)] - S- (noctylj-thiocarbonate the following acute oral LD50:

Maus ? 28,410 (23,680-34,190) mg/kg 24 Stunden undMouse ? 28,410 (23,680-34,190) mg / kg 24 hours and

7-Tage-Test
(J 32.690 (20./90-50.820) mg/kg 24-Stunden-7 day trial
(J 32,690 (20/90-50,820) mg / kg 24-hour

Testtest

ο 11.550 (9,130 - I '1,900) mg/kg
Ratte 9 2,720 (2,050-3,620) mg/kg 0-[3-Phenyl-6-chlor-pyridazinyl-(4)]-S-(n-butyl)-Thiocarbonat, η =1,5920.ο 11,550 (9,130 - I '1,900) mg / kg
Rat 9 2,720 (2,050-3,620) mg / kg of 0- [3-phenyl-6-chloro-pyridazinyl- (4)] - S- (n-butyl) thiocarbonate, η = 1.5920.

ö 2.200 (1,420-3,400) mg/kg C ber. 55,81%
gef. 55,5%ö 2,200 (1,420-3,400) mg / kg C calc. 55.81%
found 55.5%

Cl ber. 10^8%
gef. 113%Cl ber. 10 ^ 8%
found 113%

7-Tage-Test
24-Stunden- u. 7-Tage-Test
24-Stunden- u. 7-Tage-Test7 day trial
24-hour and 7-day test
24-hour and 7-day test

Die akute orale LD50 der Vergleichssubstanz 3-lsopropyl-2,l,3-benzothiadiazinon-(4)-2,2-dioxyd beträgt dagegen an Ratten 1,100 mg/kg (H. M a r t i η , Pesticide Manual, 4. Auflage, 1974, Seite 37).The acute oral LD50 of the reference substance 3-isopropyl-2, l, 3-benzothiadiazinon- (4) -2,2-dioxide on the other hand is 1.100 mg / kg in rats (H. M a r t i η, Pesticide Manual, 4th edition, 1974, page 37).

Die Herstellung der erfindungsgemäßen Verbindungen und Mittel sowie ihre Wirkungsweise im Vergleich zu bereits bekannten Mitteln soll in den folgenden Beispielen näher erläutert werden.The preparation of the compounds and compositions according to the invention and their mode of action in comparison The following examples will explain in more detail the means that are already known.

Beispiel IExample I.

1.5 Teile 3-Phenyl-4-hydroxy-6-ch!orpyridazin wurden in 8 Teilen Benzol suspendiert, mit 0,75 Teilen Triäthylamin 20 Minuten gerührt und dann in das heterogen flüssige Gemisch eine Lösung von 1,08 Teilen Chlorthioameisensäure-S-n-butylester in 2 Teilen Benzol rasch zugegeben. Dabei stieg die Temperatur der Mischung im Laufe von 2 Minuten von 22°C auf 45°C an, und feinkristallines Triäthylamin-hydrochlorid wurde gebildet. Nach zweistündiger Reaktionszeit wurden 3 Teile Wasser zugesetzt, 10 Minuten gerührt, die wäßrige Phase abgetrennt und nochmals mit I Teil Wasser ausgerührt.1.5 parts of 3-phenyl-4-hydroxy-6-chloropyridazine were suspended in 8 parts of benzene, stirred with 0.75 parts of triethylamine for 20 minutes and then into the heterogeneous liquid mixture is a solution of 1.08 parts of chlorothioformic acid S-n-butyl ester in 2 parts of benzene quickly admitted. The temperature of the mixture rose from 22 ° C. to 45 ° C. in the course of 2 minutes on, and finely crystalline triethylamine hydrochloride was formed. After a reaction time of two hours 3 parts of water were added, the mixture was stirred for 10 minutes, the aqueous phase was separated off and again with 1 part of water carried out.

Die benzolische Lösung wurde mit 0,5 Teilen Na2SÜ4 getrocknet, abfiltriert und das Filtrat im Vakuum eingedampft. The benzene solution was with 0.5 part Na2SÜ4 dried, filtered off and the filtrate evaporated in vacuo.

Es ergaben sich 2,30 Teile braun gefärbtes, öliges Produkt entsprechend einer 98%igen Ausbeute an H ber. 4,68% gef. 4,7%This gave 2.30 parts of brown, oily product, corresponding to a 98% yield H calc. 4.68% found. 4.7%

S ber. 9,93% gef. 10,1%S calc. 9.93% found. 10.1%

N ber. 8,68% gef. 8,6%N calc. 8.68% found 8.6%

Nach der im Beispiel 1 angeführten Arbeitsweise wurde 3-Phenyl-4-hydroxy-6-chlorpyridazin und das 3-Phenyl-4-hydroxy-6-brompyridazin mit den entsprechenden Chlorthioameisensäureestern umgesetzt und folgende Verbindungen erhalten:Following the procedure outlined in Example 1, 3-phenyl-4-hydroxy-6-chloropyridazine and the 3-Phenyl-4-hydroxy-6-bromopyridazine reacted with the corresponding chlorothioformic acid esters and receive the following connections:

O-ti-Phenyl-e-chlor-pyridazinyl-^JJ-S-in-propylJ-thiocarbonat O-ti-phenyl-e-chloro-pyridazinyl- ^ JJ-S-in-propylJ-thiocarbonate

70% Ausbeute η =1,596470% yield η = 1.5964

C ber. 54,55% H ber. 4,24% N ber. 9,07%C calc. 54.55% H calc. 4.24% N calc. 9.07%

-lf) gef. 54,3% gef. 4,6% gef. 8,9%- lf) found . 54.3% found 4.6% found 8.9%

Cl ber. 11,48% S ber. 10,36% gef. 11,9% gef. 10,8%Cl calculated. 11.48% S calculated. 10.36% found. 11.9% found 10.8%

O-[3-Phenyl-6-brom-pyridazinyl-(4)]-S-(n-butyl)-thiocarbonat O- [3-phenyl-6-bromo-pyridazinyl- (4)] - S- (n-butyl) thiocarbonate

51% Ausbeute η =1,603351% yield η = 1.6033

C ber. 49,05% H ber. 4,12% N ber. 7,63%C calc. 49.05% H calc. 4.12% N calc. 7.63%

j0 gef. 50,0% gef. 4.7% gef. 7,4%j 0 found . 50.0% found 4.7% found 7.4%

Br ber. 21,76% S ber. 8,73% gef. 20,7% gef. 9.4%Br calc. 21.76% S calc. 8.73% found 20.7% found 9.4%

0-[3-Phenyl-6-chlor-pyridazinyl-(4)]-S-[butyl-(2)]-thioj-, carbonat0- [3-Phenyl-6-chloro-pyridazinyl- (4)] - S- [butyl- (2)] - thioj-, carbonate

71,5% Ausbeute
C ber. 55,81%71.5% yield
C calculated 55.81%

gef. 55,6%
Cl ber. 10,98%found 55.6%
Cl calculated 10.98%

gef. 11,5%found 11.5%

η =1,5897 H ber. 4,68% N ber. 8,68% η = 1.5897 H calc. 4.68% N calc. 8.68%

gef. 5,1% gef. 8,6%found 5.1% found 8.6%

S ber. 9,93%S calc. 9.93%

gef. 11,0%found 11.0%

O-[3-Phenyl-6-chlor-pyridazinyl-(4)]-S-(n-pentyl)-thiocarbonat O- [3-Phenyl-6-chloro-pyridazinyl- (4)] - S- (n -pentyl) thiocarbonate

72,5% Ausbeute
C ber. 57,05%72.5% yield
C calculated 57.05%

gef. 57,1%
Cl ber. 10,53%found 57.1%
Cl calculated 10.53%

gef. 11,3%found 11.3%

η =1,5834 H ber. 5.09% η = 1.5834 H calc. 5.09%

gef. 5,5% S ber. 9,52%found 5.5% S calc. 9.52%

gef. 10.1%found 10.1%

N ber. 8,32% gef. 8.0%N calc. 8.32% found 8.0%

0-t3-Phenyl-6-chlor-pyridazinyl-(4)]-S-[3-methylbutyl-(l)]-thiocarbonat 0- t3-Phenyl-6-chloro-pyridazinyl- (4)] - S- [3-methylbutyl- (1)] - thiocarbonate

79% Ausbeute
C ber. 57,05%79% yield
C calculated 57.05%

gef. 57,6%
Cl ber. 10,53%found 57.6%
Cl calculated 10.53%

gef. 10,7%found 10.7%

η =1,5790 H ber. 5,09% η = 1.5790 H calc. 5.09%

gef. 5,9% S ber. 9,52%found 5.9% S calc. 9.52%

gef. 10,2%found 10.2%

N ber. 8,32% gef. 7.8%N calc. 8.32% found 7.8%

0-[3Phenyl-6-chlor-pyridazinyl-(4)]-S-(n-hexyl)-thiocarbonat 0- [3-phenyl-6-chloro-pyridazinyl- (4)] - S- (n-hexyl) thiocarbonate

71% Ausbeute η =1,571371% yield η = 1.5713

C ber. 58,19% H ber. 5,46% N ber. 7,99%C calc. 58.19% H calc. 5.46% N calc. 7.99%

gef. 57,9% gef. 6,3% gef. 7,9%found 57.9% found 6.3% found 7.9%

Cl ber. 10,11% S ber. 9,14%Cl calculated 10.11% S calculated 9.14%

gef. 10,5% gef. 9,9%found 10.5% found 9.9%

0-[3-Phenyl-6-chlor-pyridazinyl-(4)]-S-(n-heptyl)-thiocarbonat 0- [3-Phenyl-6-chloro-pyridazinyl- (4)] - S- (n-heptyl) thiocarbonate

85% Ausbeute η =1,566085% yield η = 1.5660

C ber. 59,25% H ber. 5,80% N ber. 7,68%C calc. 59.25% H calc. 5.80% N calc. 7.68%

gef. 58,9% gef. 6,1% gef. 7,2%found 58.9% found 6.1% found 7.2%

CI ber. 9,72% S ber. 8,79%CI calculated 9.72% S calculated 8.79%

gef. 10,1% gef. 9,2%found 10.1% found 9.2%

O-[3-PhenyI-6-chIor-pyridazinyl-(4)]-S-(n-octyl)-thiocarbonat O- [3-Phenyl-6-chloro-pyridazinyl- (4)] - S- (n-octyl) thiocarbonate

85% Ausbeute η =1,568985% yield η = 1.5689

C ber. 60,22% H ber. 6,12% N ber. 7,39%C calc. 60.22% H calc. 6.12% N calc. 7.39%

gef. 603% gef. 6,3% gef. 7,1%found 603% found 6.3% found 7.1%

Clber. 9,39% S ber. 8,41%Clber. 9.39% S calc. 8.41%

gef. 9,1% gef. 8,7%found 9.1% found 8.7%

O-[3-Phenyl-6-brom-pyridazinyi-(4)]-S-(n-octyl)-thiocarbonat O- [3-phenyl-6-bromo-pyridazinyi- (4)] - S- (n-octyl) thiocarbonate

87% Ausbeute η =1,577487% yield η = 1.5774

C ber. 53,90% H ber. 5,48% N ber. 6,62%C calc. 53.90% H calc. 5.48% N calc. 6.62%

gef. 55,0% gef. 5,8% gef. 6,3%found 55.0% found 5.8% found 6.3%

Br ber. 18,88% S ber. 7,57%Br calc. 18.88% S calc. 7.57%

gef. 17,7% gef. 8,0%found 17.7% found 8.0%

O-[3-Phenyl-6-chlor-pyridazinyl-(4)]-S-(n-dodecyl)-thiocarbonat O- [3-Phenyl-6-chloro-pyridazinyl- (4)] - S- (n -dodecyl) thiocarbonate

O-[3-Phenyl-6-chlor-pyridazjnyI-(4)l-O-(n-butyl)-thionocarbonat O- [3-Phenyl-6-chloropyridazynyl- (4) l- O- (n-butyl) thionocarbonate

57% Ausbeute
C ber. 55,81%57% yield
C calculated 55.81%

gef. 55,1%
Cl ber. 10,98%found 55.1%
Cl calculated 10.98%

gef. 11,3%found 11.3%

76% Ausbeute
C ber. 63,5%76% yield
C calculated 63.5%

gef. 63,2%
Cl ber. 8,15%found 63.2%
Cl calculated 8.15%

gef. 8,6%found 8.6%

η =1,5498 η = 1.5498

H ber. 7.18% gef. 8,0%H calc. 7.18% 8.0%

S ber. 7,37% gef. 7.5%S calc. 7.37% found. 7.5%

Beispiel 2Example 2

N ber. 6,44% gef. 6,2%N calc. 6.44% found 6.2%

10 Teile S-Phenyl^-hydroxy-ö-chlorpyridazin wurden in 1 Oo Teilen Benzol suspendiert, 5,2 Teile Triethylamin zugegeben, 10 Minuten gerührt, dann eine Lösung von 5,7 Teilen Chlorthionoameisensäure-O-äthylester in 20 Teilen Benzol zugegeben und 20 Minuten reagieren gelassen. Dann wurden 20 Teile Wasser zugesetzt, 5 Minuten gerührt, die wäßrige Phase abgetrennt, die benzolische Schicht mit Wasser gewaschen, mit Na2S(Xt getrocknet, filtriert, im Vakuum eingedampft und aus Petroläther umkristalliiiert. Es ergaben sich 8,7 Teile weißes Produkt entsorechend einer 61%igen Ausbeute an O-^-Phenyl-e-cnlor-pyridazinyl-^JJ-O-fäthyO-thionocarbonat. 10 parts of S-phenyl ^ -hydroxy-ö-chloropyridazine were suspended in 10 parts of benzene, 5.2 parts of triethylamine were added, the mixture was stirred for 10 minutes, then a solution of 5.7 parts of chlorothionoformic acid O-ethyl ester in 20 parts of benzene was added and Allowed to react for 20 minutes. 20 parts of water were then added, the mixture was stirred for 5 minutes, the aqueous phase was separated off, the benzene layer was washed with water, dried with Na 2 S (Xt, filtered, evaporated in vacuo and recrystallized from petroleum ether, giving 8.7 parts of white product corresponding to a 61% yield of O - ^ - phenyl-e-chloro-pyridazinyl- ^ JJ-O-fäthyO-thionocarbonate.

Fp = 77-79° C.
C ber. 52,97%Mp = 77-79 ° C.
C calc. 52.97%

gef. 52,5%
Cl ber. 12,03%found 52.5%
Cl calculated 12.03%

gef. 11,9%found 11.9%

H ber. 3,76% gef. 3,7%H calc. 3.76% found. 3.7%

S ber. 10,88% gef. 11,1%S calc. 10.88% found. 11.1%

N ber. 9,51% gef. 9,3O/oN calc. 9.51% found. 9.3O / o

Analog wurden folgende Verbindungen erhalten:The following compounds were obtained analogously:

O-[3-Phenyl-6-chlor-pyridazinyl-(4)]-O-(n-propyl)-thionocarbonat O- [3-phenyl-6-chloro-pyridazinyl- (4)] - O- (n-propyl) thionocarbonate

53% Ausbeute Fp = 58-61°C53% yield m.p. 58-61 ° C

C ber. 54,45°/o H ber. 4.24% N ber. 9,07%C cal. 54.45 ° / o H cal. 4.24% N cal. 9.07%

gef. 54.5% gef. 4,3% gef. 9,3%found 54.5% found 4.3% found 9.3%

Cl ber. 11.48% [. ber. 10,38%Cl calc. 11.48% [. ber. 10.38%

gef. 11.5% gef. 10,5%found 11.5% found 10.5%

η =1,5824
H ber. 4,68% N ber. 8,68% η = 1.5824
H calc. 4.68% N calc. 8.68%

gef. 4,7% gef. 7,9%found 4.7% found 7.9%

S ber. 9,93%S calc. 9.93%

gef. 10,2%found 10.2%

0-[3-Phenyl-6-chlor-pyridazinyl-(4)]-0-(isobutyi)-thionocarbonat 0- [3-Phenyl-6-chloro-pyridazinyl- (4)] - 0- (isobutyl) thionocarbonate

64% Ausbeute π =1,575264% yield π = 1.5752

C ber. 55,81% H ber. 4,68% N ber. 8,68%C calculated 55.81% H calculated 4.68% N calculated 8.68%

,5 gef. 55,0% gef. 5,1% gef. 8,3%, 5 found. 55.0% found 5.1% found 8.3%

CI ber. 10,98% S ber. 9,93%
gef. 11,0% gef. 10,0%CI calculated 10.98% S calculated 9.93%
found 11.0% found 10.0%

0-[3-Phenyl-6-brom-pyridazinyl-(4)]-O-(isobutyl)-
:o thionocarbonat0- [3-phenyl-6-bromo-pyridazinyl- (4)] - O- (isobutyl) -
: o thionocarbonate

45% Ausbeute η =1,583845% yield η = 1.5838

C ber. 49,05% H ber. 4,12% N ber. 7,63%C calc. 49.05% H calc. 4.12% N calc. 7.63%

gef. 48,7% gef. 4,4% gef. 7.2%found 48.7% found 4.4% found 7.2%

r, Br t-.r. 21,76% S ber. 8.73%r, Br t-.r. 21.76% S calc. 8.73%

gef. 22,1% gef. 9,0%found 22.1% found 9.0%

O-[3-Phenyl-6-chlor-pyridazinyl-(4)]-O-(n-hexyl)-thionocarbonat O- [3-phenyl-6-chloro-pyridazinyl- (4)] - O- (n-hexyl) thionocarbonate

72% Ausbeute η =1.560572% yield η = 1.5605

C ber. 58,19% H ber. 5,46% N ber. 7.99%C calculated 58.19% H calculated 5.46% N calculated 7.99%

gef. 58,1% gef. 6,1% gef. 7.8%found 58.1% found 6.1% found 7.8%

Cl ber. 10.11% S ber. 9.14%
r> gef. 10,1% gef. 9,3%Cl calculated 10.11% S calculated 9.14%
r> found. 10.1% found 9.3%

Beispiel 3Example 3

20Teile 3-Phenyl-4-hydroxy-6-chlorpyridazin wurden in 180 Teilen Benzol suspendiert. 9 Teile Pyridin zugegeben, 10 Minuten gerührt und zu der Suspension 14 Teile Chlorthioameisensäure-S-n-butylester zugegeben und 1 Stunde gerührt. Dann mit 50 Teilen Wasser 1 Minute geschüttelt, die wäßrige Phase abgetrennt, die benzolische Lösung getrocknet und eingedampft. Es ergaben sich 28 Teile gelbes öl entsprechend einer 89%igen Ausbeute an O-[3-Phcnyl-6-chlor-pyridazinyl-(4)]-S-(n-butyl)-thiocarbonat. 20 parts of 3-phenyl-4-hydroxy-6-chloropyridazine were suspended in 180 parts of benzene. 9 parts of pyridine were added, the mixture was stirred for 10 minutes and added to the suspension 14 Parts of chlorothioformic acid S-n-butyl ester were added and stirred for 1 hour. Then shaken with 50 parts of water for 1 minute, the aqueous phase separated, the benzene solution dried and evaporated. There were 28 parts of yellow oil corresponding to one 89% yield of O- [3-phenyl-6-chloro-pyridazinyl- (4)] - S- (n-butyl) thiocarbonate.

η =1,5896. η = 1.5896.

Verwendungsbeispiel 1Usage example 1

20 Teile O-[>Phenyl-6-chlor-pyridazinyl-(4)]-S-(r butyl)-thiocarbonat, 70 Teile Xylol und 10 Teile Alkylarylsulfonat in Mischung mit Polyoxyäthylen-Sorbitan-TallöL ster wurden vermengt. Das Emulsionskonzentrat ergab durch Einrühren in eine zur Applikation auf die Pflanze erforderliche Wassermenge eine stabile Emulsion.20 parts of O - [> Phenyl-6-chloro-pyridazinyl- (4)] - S- (r butyl) thiocarbonate, 70 parts of xylene and 10 parts of alkylarylsulfonate in a mixture with polyoxyethylene sorbitan tall oil they were mixed up. The emulsion concentrate produced by stirring into an amount of water required for application to the plant stable emulsion.

Anwendungsbeispiel 2Application example 2

50 Teile O-f3-Phenyl-6-chlorpyriaa.'.inyl-(4)]-S-(n-butyl)-thiocarbonat. 43 Teile Xylol und 7 Teile Alkylaryisulfonat in Mischung mit Polyoxyäthylen-Sorbitan-Tallölester wurden vermengt. Das Emulsionskonzentrat ergab durch Einrühren in Wasser eine stabile Emulsion. Alle weiteren erfindungsgemäßen Mittel wurden ähnlich formuliert.50 parts of O-f3-phenyl-6-chloropyriaa. '. Ynyl- (4)] - S- (n-butyl) thiocarbonate. 43 parts of xylene and 7 parts of alkylaryisulfonate in a mixture with polyoxyethylene sorbitan tall oil ester were mixed up. The emulsion concentrate produced a stable emulsion when stirred into water. All other agents according to the invention were formulated similarly.

Verglcii hsversiich ICompared to I

Die in den Tabellen enthaltenen, crfindungsgeniiißen Verbindungen wurden in ihrer herbiziden Wirksamkeit und Kuluirpflan/enverträglichkcit verglichen mitThe foundations contained in the tables have been found Compounds were compared in their herbicidal effectiveness and Kuluirpflan / enverträglichkit with

a) 2■ Phcnyl-4-brom-5-{>xaloaminop\ndazon-(3)-Na a) 2 ■ Phcnyl-4-bromo-5 - {> xaloaminop \ ndazon- (3) -Na

b) 2-Phcnyl-4-brom-5-(\-hydroxy-/?./J.p-lrichloräthylamino)-pyndazon-(3) b) 2-Phcnyl-4-bromo-5 - (\ - hydroxy - /? ./ J.p-lrichloräthylamino) -pyndazon- (3)

c) 2· Phenyl-5-isobutvry lam ino-4-brompyrida/.on-(3) c) 2 · phenyl-5-isobutvry lam ino-4-brompyrida / .on- (3)

d) 3lsopropyl-2.1.3-bcnzothiadiazinon-(4)-2.2-dumd d) isopropyl-2.1.3-bcnzothiadiazinon- (4) -2.2-dumd

a)-d) aus R. W e g I e r. Vol. 2. 1970. Seite 350. 351 und 359a) -d) from R. W e g I e r. Vol. 2. 1970. page 350. 351 and 359

e) 3-Phenyl-4-hydroxy-6-chlorpyridazin aus
Di .()s ->\ ?q irw ,mr|e) 3-phenyl-4-hydroxy-6-chloropyridazine from
Di. () S -> \ ? Q irw, mr |

f) 3.4.6-Tridilor-5-äthoxypyridazin aus
DR-C)S 17 70 828.f) 3.4.6-Tridilor-5-ethoxypyridazine from
DR-C) S 17 70 828.

Methode:Method: ReiherschnabelHeron beak = Λ= Λ RainkohlRain cabbage = B= B Im Gewächshaus herangezogene UnkräuterWeeds grown in the greenhouse KlettenlabkrautBurdock weed F.rodium citutariumF.rodium citutarium AckerhundskamilleField dog chamomile = D= D l.apsana conimunisl.apsana conimunis Rote TaubnesselRed dead nettle = E= E Cialiiim apanneCialiiim apanne StengelumfassendeStalk encompassing = F= F Arthemis arvensisArthemis arvensis TaubnesselDead nettle I.annum purpureumI. annum purpureum VogelmiereChickweed = G= G Laminin amnie\icauleLaminin amnie \ icaule F.feublättrigerF. fey leaved = Fl= Fl EhrenpreisHonorary award Stellarij mediaStellarij media Persischer EhrenpreisPersian Speedwell = I= I. \ er'inica hederil'olia\ er'inica hederil'olia Gemeiner HohlzahnCommon hollow tooth = K= K Bunter HohlzahnColorful hollow tooth = 1.= 1. Veronica nersieaVeronica nersiea FranzosenkrautFrench herb = M= M G.iieopsis tetrahitG.iieopsis tetrahit Hederichwild radish = N= N Galeonsis speciosaGaleonsis speciosa Cj.iiin^ita pan. ifloraCj.iiin ^ ita pan. iflora RaphcinusRaphcinus

wurden, nachdem die Unkräuter das 4- bis b-lilattstaditim erreicht hallen, mit einer Suspension der zu Prüfenden Verbindungen besprüht. Zu diesem Zwecke wurden die Wirkstoffe in eine spritzfähige Form gebracht, und zwar kamen jeweils Spritzpulver folgender Zusammensetzung zur Anwendung:after the weeds passed the 4- to b-lilattstaditim reached halls, sprayed with a suspension of the compounds to be tested. For this purpose the active ingredients were brought into an injectable form, namely wettable powder in each case the following composition for use:

50Gew.-% der jeweiligen Aktivsubsianz50% by weight of the respective active subsidy

2 Gew.-% Alkylarylsulfonsaures Na2% by weight of alkylarylsulfonic acid Na

4 Gew.-n/n Na-Oleyl-methyl-taurid und4 wt. N / n Na oleyl methyl tauride and

44 Gew.-% Kieselsäure44 wt% silica

Die Konzentralionen der Spritzflüssigkeit wurden so gewählt, daß Wirkstoffmengen von 0.3,0.6 und 1,2 kg/ha sich ergaben. (Spritzbrühenaufwand 40 ml/m-', entsprechend 400 l/ha.)The concentrations of the spray liquid were chosen so that active ingredient quantities of 0.3, 0.6 and 1.2 kg / ha surrendered. (Spray mixture consumption 40 ml / m- ', corresponding to 400 l / ha.)

In einer weiteren Versuehsseric wurden Gräser ausIn a further experiment, grasses were made

der Gruppe tici »Wildi'i'ii'Scn« (VvCitVCrbrCitCiC Ungräser in Maiskullurcn) im Gewächshaus in Kunststofftöpfen herangezogen, und zwar:of the group tici »Wildi'i'ii'Scn« (VvCitVCrbrCitCiC grass weeds in corn husks) in the greenhouse in plastic pots used, namely:

Echinochloa crus galli
Setaria viridis
Digitaria sanguinalc
Digitaria filiformisEchinochloa crus galli
Setaria viridis
Digitaria sanguinalc
Digitaria filiformis

I lühnerhirse = C)I lühner millet = C)

Grüne Borstenhirse = PGreen millet = P

Bluthirse = 0Blood millet = 0

Fadenfingerhirsc = RThread-fingerhirsc = R

Diese Un'.rüuter wurden, nachdem sie das 3- bis 4-Blattstadium erreicht halten, mit Suspensionen der zu prüfenden Verbindungen besprüht. Die Konzentrationen der Spritzflüssigkeit wurden .:o gewählt, daß Wirkstoffmengen von 0.5. 1.0 und 1.5 kg/ha ausgebracht wurden (Brühenaufwand 40 ml/m-', entsprechend 400 l/ha).These Un'.ruuter were after they 3 to Hold reached 4-leaf stage, with suspensions of the too testing connections sprayed. The concentrations of the spray liquid were chosen: o that Active ingredient amounts of 0.5. 1.0 and 1.5 kg / ha were applied (brewing expenditure 40 ml / m- ', accordingly 400 l / ha).

Nach 14 Tagen (dikotyle Unkräuter) bis 3 Wochen (Wildhirsen) wurde der herbizide Effekt gemäß dem E.W.R.C.-Bonitierungsschema (E.W.R.C. = European Weed Research Council) ermittelt. Den Wertzahlen 1 bis 9 entsprechen folgende Abtötungs- bzw. Schädigungsraten: After 14 days (dicot weeds) to 3 weeks (wild millet) the herbicidal effect was according to the E.W.R.C. rating scheme (E.W.R.C. = European Weed Research Council). The numerals 1 to 9 correspond to the following kill and damage rates:

Werzah! der herbiz'.den
WirkungWerzah! the herbiz'.den
effect Entsprechend
Prozent
Abtötung der
UnkräuterCorresponding
percent
Killing the
Weeds Wertzahl der Schädigung der
KulturpflanzenValue of the damage to the
Crops Entsprechend
Prozent Aus
dünnung bzw
Wuchs
hemmungCorresponding
Percent off
thinning or
growth
inhibition i ausgezeichneti excellent 100100 1 keine Schädigung1 no damage 00 2 sehr gut2 very good 97.597.5 2 eben merkliche Schädigung2 just noticeable damage 2.52.5 3 gut3 good 9595 3 sehr schwache Schädigung3 very slight damage 55 4 befriedigend4 satisfactory 9090 4 schwache Schädigung4 weak damage 1010 5 noch ausreichend5 is still sufficient 8585 5 mäßige Schädigung5 moderate damage 1515th 6 nicht ausreichend6 not sufficient 7575 6 starke Schädigung6 severe damage 2525th 7 gering7 low 6565 7 sehr starke Schädigung7 very severe damage 3535 8 sehr gering8 very low 32,532.5 8 äußerst starke Schädigung8 extremely severe damage 67,567.5 9 keine Wirkung9 no effect 00 9 totale Schädigung9 total damage 100100

Die Ergebnisse sind in den folgenden Tabellen zusammengefaßt Daraus geht hervor, daß die erfindungsgemäßen Verbindungen selbst bei der sehr geringen Aufwandmenge von 03 kg Aktivsubstanz/ha gegen ein breites Unkrautspektrum noch ausgezeichnet bis ausreichend wirksam sind. Im Gegensatz dazu sind die bereits vorbeschriebenen Pyridazon-Derivate (Verbindungen a. b, c) wesentlich schwächer wirksam und zeigen auch bei der höchsten Aufwandmenge erhebliche Wirkungslücken gegen dikotyle Unkräuter und sind gegen monokotyle Unkräuter (»Wildhirsen«) unwirksam. Die Verbindung d) besitzt ein wesentlich engeresThe results are summarized in the following tables. It follows that the invention Compounds even at the very low application rate of 03 kg active substance / ha against one broad spectrum of weeds are still excellent to sufficiently effective. In contrast, the Pyridazone derivatives already described above (compounds a. b, c) much less effective and show considerable even at the highest application rate Gaps in effectiveness against dicotyledon weeds and are ineffective against monocotyledon weeds ("wild millet"). The connection d) has a much narrower one

Wirkiingsspektrum, insbesondere werden wirtschaftlich bedeutsame Unkräuter, wie Taubnessel-, Ackerhohl-/ahn- und F.hrenpreisarten nicht oder schlecht erfaßt. Eine Wirkung gegen Wildhirsen fehlt völlig. Die Verbindungen e) und f) sind insgesamt wesentlichEffective spectrum, in particular, are economical significant weeds, such as dead nettle, field hollow / ahn- and honorary award types not or poorly recorded. There is absolutely no effect against wild millet. The connections e) and f) are material overall

IOIO

schwächer wirksam als die erfindungsgemaßcn Verbindungen, eine Wirkung gegen Wildhirsen fehlt ebenfalls. less effective than the compounds according to the invention, and there is also no activity against wild millet.

Für die nachfolgenden Tabellen wird die allgemeine Formel I der erfindiingsgcmäßen Verbindungen alsFor the tables below, the general formula I of the compounds according to the invention is used as

.V|'henvl-r.-llal-4-/() C Y R\ l'vr X.V | 'henvl-r.-llal-4 - / () C Y R \ l'vr X

geschrieben, wobei Ph = Phenyl und Pyr= Pyridazin bedeuten.written, where Ph = phenyl and Pyr = pyridazine.

Wirk- Herbizide Wirkung gegen dikotyle Unkräuter (1—9) stoff,Active herbicidal effect against dicotyledon weeds (1—9) substance,

Wirk- Wirkung gegen stoff, monokotyle Unkr.: ke/ha »Wildhirsen« (1-9)Active effect against substance, monocotyledonous species: ke / ha »wild millet« (1-9)

IVIV 1,21.2 AA. :: 11 II. II. KK LL. MM. NN 1,51.5 OO PP. QQ RR. M Γ Υ Rj
ν I M Γ Υ Rj
ν I 0,60.6 11 2 ' 2 ' 11 II. 11 11 11 11 1,01.0 11 22 11 22 ■ * /
Thiolcarbonate■ * /
Thiol carbonates 0,30.3 11 11 11 11 11 11 33 0,50.5 44th 44th 44th 55 (X = O, Y = S)(X = O, Y = S) 1,21.2 11 11 22 11 33 33 11 55 1,51.5 99 99 99 99 HalogenidHalide 0,60.6 11 11 11 II. 11 II. 11 1,01.0 11 11 11 11 R-R- 0,30.3 11 11 11 11 22 11 33 0,50.5 33 33 44th 44th methylmethyl 1,21.2 11 Z D Z D 11 33 33 44th 22 44th 1,51.5 99 99 99 99 0,60.6 11 11 11 11 11 11 11 11 11 1,01.0 11 11 11 tt 0,30.3 11 11 11 II. 11 11 11 11 33 0,50.5 33 22 33 44th n-propyln-propyl 1,21.2 11 33 11 22 33 22 33 11 55 1,51.5 99 99 99 99 0,60.6 11 11 11 11 11 11 11 11 11 1,01.0 11 11 11 11 0,30.3 11 11 11 11 11 11 11 11 33 0,50.5 33 33 22 22 iso-propyliso-propyl 1,21.2 11 22 I 1I 1 33 33 33 33 11 55 1,51.5 99 99 99 0,60.6 11 11 11 11 11 11 11 11 11 1,01.0 11 11 11 11 0,30.3 11 1 11 1 11 11 11 11 II. 33 0,50.5 33 33 33 44th n-butyln-butyl 1,21.2 11 22 11 55 44th 55 11 55 1,51.5 99 99 99 99 0,60.6 11 11 11 11 11 11 11 11 1,01.0 11 11 11 11 0,30.3 1 ^1 ^ 11 11 ■>■> 11 11 11 11 44th 0,50.5 55 55 55 44th sec-butylsec-butyl 1,21.2 1 f1 f 44th j :j: )) 11 55 55 11 55 1,51.5 99 99 99 99 0,60.6 11 11 11 11 11 11 11 1,01.0 11 11 22 22 0,30.3 11 11 11 11 22 11 44th 0,50.5 44th 55 55 55 tert.-butyltert-butyl 11 33 11 44th 44th 11 66th 1313th 99 99 99 99 0,60.6 11 11 11 11 11 11 11 1,01.0 11 11 11 11 0303 11 > 3> 3 - G- G 11 11 22 11 33 0303 44th 44th 44th 55 n-amyln-amyl UU 11 1 41 4 11 ιι 44th 44th 44th 11 55 1313th 99 99 99 99 0,60.6 11 11 33 11 11 11 11 11 1,01.0 22 22 22 22 0303 11 11 55 11 11 11 11 22 0303 44th 55 55 55 iso-amyliso-amyl 1,21.2 11 22 11 11 22 22 11 44th 1313th 99 99 99 99 0,60.6 11 11 22 11 11 11 11 11 1,01.0 11 22 33 22 0303 11 11 55 11 11 22 11 44th 0303 44th 55 66th 55 n-hexyln-hexyl 1,21.2 11 33 11 11 33 33 11 55 1313th 99 99 99 99 0,60.6 11 11 22 11 11 11 11 11 1,01.0 11 11 11 11 0303 11 11 44th 11 11 11 11 22 0303 22 33 33 22 n-heptyln-heptyl 11 33 11 11 33 44th 11 55 1313th 77th 99 99 99 0,60.6 11 11 11 11 11 11 11 11 1,01.0 22 33 22 22 0303 11 22 44th ιι 22 11 11 11 44th 0303 33 44th 55 55 n-octyln-octyl ι :ι: 55 11 \\ 55 55 55 55 66th 99 99 99 99 11 44th 11 6 '6 ' n-dodecyln-dodecyl 33 11 11 11 3 <3 < } 3} 3 6 ,6, t 5 :t 5: 11 22 66th 11 11 E IE I 5 :5: 11 11 11 11 55 11 22 55 11 [[ 11 11 55 11 \ :\: 3 ;3; ( 5 ' (5 ' II. ιι II. II.

> Γ> Γ i-ii-H.iM-i-ii-H.iM- Wirk- Herbizide WirkungActive herbicidal effect l'\rl '\ r AA. B CB C DD. gegenagainst dikotyle Unkräuterdicot weeds HH I II I (1-9)(1-9) MM. NN WirkReally Wirkungeffect gegenagainst iVildhirsen«
— 9)iVild millet «
- 9) QQ Unkr.Uncommon WildhirsenWild millet UnkrUncommon stoff,material, 1.2 11.2 1 1 11 1 11 11 11 II. 11 stoff.material. monokotylemonocot 11 1-9)1-9) kg/hakg / ha 0,6 10.6 1 2 I2 I. 33 33 2 : 2 : II. 33 kg/hakg / ha »1
(1 "1
(1 44th 0,3 10.3 1 4 24 2 44th 44th 4 i 4 i 44th 55 99 O ( Y R O (Y R 1.2 11.2 1 1 11 1 11 11 11 II. 11 11 ThiolcarbonateThiol carbonates 0,6 10.6 1 1 11 1 11 11 11 11 33 PP. 33 (X = O, Y = S)(X = O, Y = S) O1J 1O 1 J 1 ii 22 ii ii ii 55 11 99 RR. Halogen = BrHalogen = Br 1,2 11.2 1 1 11 1 11 EE. - G- G 11 11 C LC L 11 II. OO 44th 11 11 R: "R: " 0,6 10.6 1 1 11 1 11 11 II. 11 11 11 11 44th 1,51.5 11 99 33 44th methylmethyl 0,3 10.3 1 I II I 33 ]] 44th 22 33 > 2> 2 11 66th 1,01.0 44th 11 99 99 1.2 11.2 1 1 11 1 11 3 :3: Ϊ 6 Ϊ 6 11 11 ) 5) 5 11 11 0,50.5 99 22 22 11 0,6 10.6 1 1 11 1 11 11 11 11 11 11 II. 44th 1,51.5 11 99 55 22 äthylethyl 0,3 10.3 1 1 11 1 33 11 11 11 3 .3. 11 11 55 1,01.0 22 11 99 33 1,2 11.2 1 1 11 1 11 ii 55 11 11 44th 11 11 0,j0, j 77th 22 22 11 0,6 10.6 1 1 11 1 11 11 11 11 11 11 11 44th 1,51.5 11 99 55 33 iso-propyliso-propyl 0,3 10.3 1 1 11 1 44th 11 22 11 ι :ι: 11 22 66th 1,01.0 22 22 99 99 1,2 11.2 1 11 11 11 55 11 II. 44th 11 11 0,50.5 77th 55 33 22 0,6 10.6 1 1 11 1 22 11 11 11 ι ;ι; 11 11 33 1,51.5 22 99 66th 55 n-butyln-butyl 0,3 10.3 1 3 33 3 44th 11 11 11 1 ' 1 ' 11 44th 44th 1,01.0 44th 22 99 99 1,2 11.2 1 I II I 11 11 33 11 11 J 4J 4 11 11 0,50.5 99 44th 55 11 0,6 10.6 1 1 21 2 22 11 11 22 33 11 11 33 1,51.5 22 99 55 44th iso-butyliso-butyl 0,3 10.3 1 4 34 3 44th 11 22 44th 4 ' 4 ' 22 33 55 1,01.0 44th 33 99 99 Wirk- Herbizide WirkungActive herbicidal effect 11 33 gegen dikotyle Unkräuteiagainst dicot weed eggs 2 32 3 0,50.5 99 55 33 stoff,material, 11 11 11 1,51.5 33 99 55 n-octyln-octyl kg/hakg / ha 11 33 2 22 2 1,01.0 55 55 99 3 .3. 3 53 5 \ 4 \ 4 0,50.5 99 66th 44th 11 11 11 1414th 44th 99 55 n-dodecyln-dodecyl 11 2 42 4 i 3 i 3 1,01.0 66th Wirkungeffect 99 3 .3. 3 53 5 i 5 i 5 0,50.5 99 gegenagainst (1-9)(1-9) WirkReally monokoiylemonocoye 3-Hi-f.-H.il-4- -3-Hi-f.-H.il-4- - stoff,material, »» kg/hakg / ha ((

O C YRO C YR

Thionocarbonate (X = S, Y = O) Halogen = CI R^Thionocarbonates (X = S, Y = O) halogen = CI R ^

M NM N

O PO P

äthylethyl

n-propyl n-butyl iso-butyl n-hexyln-propyl n-butyl iso-butyl n-hexyl

1,2 11.2 1 1 11 1 11 11 11 11 11 11 11 11 11 1,51.5 11 11 22 11 0,6 10.6 1 3 33 3 22 22 22 55 2 ;2; 3 33 3 33 11 33 1,01.0 44th 33 44th 44th 03 303 3 5 65 6 55 44th 44th 66th 5 .5. 5 55 5 44th 33 55 0404 99 99 99 99 U 1U 1 1 11 1 11 11 11 11 11 I 1I 1 11 11 11 1414th 11 11 11 11 0,6 10.6 1 1 11 1 22 11 11 11 11 22 22 22 22 1,01.0 55 33 44th 44th 03 103 1 1 21 2 33 22 22 33 11 44th 44th 33 55 0404 99 99 99 99 1,2 11.2 1 1 11 1 11 11 11 11 11 11 11 11 11 1414th 11 11 11 11 0,6 10.6 1 1 11 1 11 11 11 11 11 22 22 11 11 1,01.0 22 33 22 22 03 103 1 1 11 1 33 11 11 33 11 44th 55 44th 55 0404 99 99 99 99 1,2 11.2 1 1 11 1 11 11 11 11 11 11 11 11 11 1414th 22 22 22 22 0,6 10.6 1 1 11 1 11 II. 11 11 11 11 11 22 22 1,01.0 55 55 55 55 03 103 1 1 11 1 33 11 11 44th 11 33 44th 44th 55 0404 99 99 99 99 1,2 11.2 1 1 11 1 11 11 11 11 ii ii 11 11 11 1414th 22 22 22 22 0,6 10.6 1 1 11 1 33 11 11 11 11 22 22 11 33 1,01.0 55 55 55 44th 03 103 1 1 11 1 44th 11 11 33 ι :ι: I 4 I 4 55 11 55 0404 99 99 99 99

R. Wegler
Vol.2. 1970R. Wegler
Vol.2. 1970

WirkReally HerbizideHerbicides BB. Wirkungeffect DD. gegen dikotyleagainst dicots FF. GG Unkräuter (IWeeds (I. II. KK -9)-9) MM. NN WirkReally Wirkung gegenEffect against stoff.material. 33 22 66th 33 11 44th 33 33 stoff.material. monokotyle Unkmonocot Unk kg/hakg / ha 66th 44th 77th 66th 33 77th 55 55 kg/hakg / ha »Wildhirsen«
(1 ·-9)"Wild millet"
(1 · -9) ΛΛ 77th CC. 77th EE. 99 77th IlIl 44th 88th I.I. 77th 66th OPQROPQR 1.21.2 11 55 88th 33 66th 66th 11 11 11 44th 44th 22 33 1,51.5 unwirksamineffective 0,60.6 33 66th 99 55 88th 77th 44th 33 22 77th 88th 44th 66th 1.01.0 0,30.3 55 77th 99 66th 99 77th 66th 66th 55 88th 99 55 77th 0.50.5 1,21.2 11 44th 66th 55 66th 44th 55 11 66th 99 44th 66th 44th 1.51.5 unwirksamineffective 0,60.6 33 77th 77th 77th 77th 77th 66th 33 77th 99 77th 66th 66th 1.01.0 0,30.3 44th 99 88th 99 88th 99 99 55 88th 99 99 88th 88th 0,50.5 1,21.2 22 11 99 11 44th 66th 11 88th 33 77th 99 11 11 1.51.5 unwirksamineffective 0,60.6 66th 11 99 11 77th 77th 11 88th 55 77th 99 11 11 1,01.0 0,30.3 99 44th 99 22 99 99 33 99 77th 88th 99 33 33 0,50.5 1.21.2 11 11 11 11 77th 11 11 33 11 44th 66th 11 11 1,51.5 unwirksamineffective 0,60.6 11 33 11 55 88th 55 55 55 11 66th 77th 44th 66th 1,01.0 0,30.3 11 66th 22 88th 99 77th 66th 77th 55 88th 99 88th 88th 0,50.5 1,21.2 11 22 11 33 11 22 33 11 33 66th 44th 22 22 1.51.5 unwirksamineffective 0,60.6 11 66th 33 66th 44th 55 66th 33 44th 77th 66th 44th 77th 1,01.0 0.30.3 33 77th 77th 88th 66th 77th 77th 66th 55 88th 88th 66th 88th 0,50.5 1,21.2 11 66th 33 33 66th 1,51.5 unwirksamineffective 0.60.6 44th 88th 66th 55 77th 1,01.0 0,30.3 55 99 77th 77th 99 0.50.5

Vergleichsversuch 2Comparative experiment 2

Prüfung der Kulturpflanzenverträglichkeit. Methode:
Im Gewächshaus herangezogene NutzpflanzenTesting of crop plant tolerance. Method:
Useful plants grown in the greenhouse

Triticum vulgäre WeizenTriticum vulgar wheat

Hordeum sativum GersteHordeum sativum barley

Avena sativa HaferAvena sativa oats

Seeale cereale RoggenSeeale cereale rye

Zea mays MaisZea mays corn

Spinacea oleracea SpinatSpinacea oleracea spinach

Vicia faba PferdebohneVicia faba horse bean

Beta vulgaris Zuckerrübe Raphanus sativus var. radicula RadieschenBeta vulgaris sugar beet Raphanus sativus var. Radicula radishes

wurden, nachdem die Getreidearten und der Mais 4 Blätter ausgebildet und die übrigen Kulturpflanzen neben den Keimblättern 3 bis 4 echte Laubblätter entwickelt hatten, mit einer Suspension der zu prüfenden Verbindungen besprüht. Die Konzentration der Spritzflüssigkeit wurde so gewählt, daß bei einem Brühenaufwand von 40 ml/m2 (entsprechend 400 l/ha) 1,5 kg/ha der aktiven Verbindung aufgebracht wird. Nach 14 Tagen wurde der Schädigungsgrad an den Pflanzen an Hand des E.W.R.C.-Schemas (1 -9) ermittelt.were, after the cereals and maize had developed 4 leaves and the remaining crop plants in addition to the cotyledons 3 to 4 true leaves, sprayed with a suspension of the compounds to be tested. The concentration of the spray liquid was chosen so that with a brewing rate of 40 ml / m 2 (corresponding to 400 l / ha) 1.5 kg / ha of the active compound is applied. After 14 days, the degree of damage to the plants was determined using the EWRC scheme (1-9).

Die Ergebnisse sind in den folgenden Tabellen zusammengefaßt. Es zeigt sich, daß die crfindungsgcmäßen Verbindungen ebenso wie die Vergleichssubstanzen für Kulturpflanzen aus der Familie der Gräser (Getreidearten) sehr gut verträglich sind. Die zu den dikotylen Gewächsen zählenden Nutzpflanzen werden von allen Verbindungen stark geschädigt oder vernichtet. Lediglich die Verbindungen a. b. c werden auf Grund ihrer nahen chemischen Verwandtschalk mit dem Rübenherbizid »Pyramin« von ,ί-Rüben toleriert. Die Verträglichkeit für bestimmte Kulturpflanzen ist allerdings nur dann von Wert, wenn auch die in diesen Kulturen vorkommenden Unkräuter verläßlich erfaßt werden. Wie aber aus Vergleichsversuch 1 ersichtlich. sind die Vergleichsverbindungen entweder insgesatm schwächer wirksam (Verbindungen a. b. c. e. f) als die erfindungsgemäßen Verbindungen oder haben Wirkungslücken (Verbindung d).The results are summarized in the following tables. It turns out that the Compounds as well as the comparison substances for cultivated plants from the grass family (Types of grain) are very well tolerated. The useful plants belonging to the dicotyledonous plants become severely damaged or destroyed by all connections. Only the connections a. b. c are due their close chemical relatives rogue with the beet herbicide »Pyramin« from. beets tolerated. the However, tolerance for certain crops is only of value if those in these crops are also of value occurring weeds can be reliably detected. But as can be seen from Comparative Experiment 1. the comparison compounds are either overall less effective (compounds a. b. c. e. f) than the Compounds according to the invention or have gaps in action (compound d).

Thiolcarbonate
(X = O1Y = S)Thiol carbonates
(X = O 1 Y = S) methylmethyl Kulturpflanzen verträglichkeit (Wertzahlen 1—9)Crop plant compatibility (numerals 1—9) HordeumHordeum AvenaAvena Seeale ZeaSeeale Zea SpinaceaSpinacea ViciaVicia Betabeta RaphanusRaphanus n-propyln-propyl TriticumTriticum sativumsativum sativ.sativ. cereal. mayscereal. mays oleraceaoleracea fabafaba vulg.vulg. sativussativus Halogen: ClHalogen: Cl iso-propyliso-propyl vulgärevulgar R:R: n-butyln-butyl sea-butylsea-butyl 11 11 99 88th 99 88th tert-butyltert-butyl 11 11 11 99 99 99 88th n-amyln-amyl 11 11 11 99 99 99 88th 11 11 11 99 99 99 99 ii 11 11 99 99 99 99 11 11 11 99 99 99 99 11 11 11 99 99 99 99 11 11 11 11 11 11 I 1I 1 I 1I 1

Thiolcarbonate
(X = O1Y = S) Thiol carbonates
(X = O 1 Y = S) methylmethyl äthyiäthyi iso-butyliso-butyl Kulturpflanzenvenräglichkeit (WertzahlenCrop plant compatibility (figures Hordeum Avena SecaleHordeum Avena Secale \vena Secale\ vena Secale 11 ereal.ereal. 11 1-9)1-9) SpiiiaceaSpiiiacea ViciaVicia Betabeta RaphanusRaphanus äthylethyl n-propyln-propyl Vergleichs-Comparative TriiicumTriiicum sativum sativ. cereal.sativum sativ. cereal. aus. ιthe end. ι 11 11 ZeaZea oleraceaoleracea fabafaba vulg.vulg. sativussativus Halogen: ClHalogen: Cl iso-propyiiso-propyi n-buty!n-buty! substanzensubstances vulgärevulgar maysmays iso-amyliso-amyl n-butyln-butyl iso-butyl iso-butyl a)a) 11 99 99 99 yy n-hexyln-hexyl iso-butyliso-butyl n-hexyln-hexyl b)b) 11 11 11 99 99 99 99 n-heptyln-heptyl n-octyin-octyi Halogen: BrHalogen: Br c)c) 11 11 99 99 99 99 n-octyln-octyl n-dodecy!n-dodecy! R:R: d)d) 11 11 99 99 99 99 n-dodecyln-dodecyl ThionocarbonateThionocarbonates e)e) 11 11 88th 66th 99 77th Halogen: BrHalogen: Br (X = S. Y = O)(X = S. Y = O) f)f) 11 R:R: 11 99 99 88th 77th Halogen: ClHalogen: Cl 11 11 99 99 99 99 R:R: 11 11 99 99 99 88th ιι 11 99 99 99 88th 11 ii 99 99 99 99 11 11 99 99 99 99 11 11 88th 77th 99 77th 11 Kui'jrp;"!.Kui'jrp; "!. ii SpinaceaSpinacea ViciaVicia Betabeta RaphanuRaphanu Tr:;: cumTr:;: cum oleraceaoleracea "aba"aba vulg.vulg. sativu'jsativu'j vulgärevulgar 1-9)1-9) 88th 88th 99 88th ·.·. 88th 88th 99 88th !! ZeaZea 99 88th 99 88th ;; ma>sma> s 88th 88th 99 88th 88th 88th 88th 88th 99 88th 99 88th 66th 55 22 66th 11 66th 55 22 66th '■'■ 66th 55 22 66th 99 66th 99 99 11 99 66th 99 77th II. 99 66th 99 77th 11 nzenverträglichkeit (Wertzahlencompatibility (value numbers HordeumHordeum sativjnisativjni 11 ]] 11

Claims (1)

Patentansprüche:Patent claims: 1. Ester von S-PhenyM-hydroxy-ö-halogen-pyridazinverbindungen der allgemeinen Formel1. Esters of S-PhenyM-hydroxy-ö-halo-pyridazine compounds the general formula O—O- Y-RY-R HaiShark N-NN-N
DE2331398A 1973-06-20 1973-06-20 Esters of S-PhenyM-hydroxy-e-halopyridazine compounds, their preparation and herbicidal compositions containing them Expired DE2331398C3 (en)

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DE2331398A DE2331398C3 (en) 1973-06-20 1973-06-20 Esters of S-PhenyM-hydroxy-e-halopyridazine compounds, their preparation and herbicidal compositions containing them
AT566173A AT326137B (en) 1973-06-20 1973-06-27 PROCESS FOR PRODUCING NEW 3-PHENYL-6-HALOGEN-PYRIDANCINE COMPOUNDS
AT566273A AT326409B (en) 1973-06-20 1973-06-27 HERBICIDAL AGENT
AR254304A AR205890A1 (en) 1973-06-20 1974-01-01 HERBICIDAL COMPOSITION TO SELECTIVELY COMBAT BAD HERBS IN USEFUL PLANT CROPS
CS3798A CS172993B2 (en) 1973-06-20 1974-05-28
YU1553/74A YU39604B (en) 1973-06-20 1974-06-04 Process for obtaining new 3-phenyl-6-halopyridazine
HU74CE1003A HU173167B (en) 1973-06-20 1974-06-07 Herbicide compositions containing phenylpyridazine compounds
GB2550574A GB1441056A (en) 1973-06-20 1974-06-07 Phenyl-pyridazines their preparation and use as herbicides
FR7419919A FR2234296B1 (en) 1973-06-20 1974-06-10
DK312374A DK137724C (en) 1973-06-20 1974-06-12 PHENYLPYRIDAZINES FOR USE IN HERBICIDES
CA202,269A CA1013745A (en) 1973-06-20 1974-06-12 Phenylpyridazines and a process for preparing same
ZA00743763A ZA743763B (en) 1973-06-20 1974-06-12 Phenylpyridazines, their preparation and use as herbicides
IL45037A IL45037A (en) 1973-06-20 1974-06-14 O-(3-phenyl-6-halo-pyridazin-4-yl)-thio-carbonate esters their preparation and herbicidal compositions containing them
CH819074A CH585013A5 (en) 1973-06-20 1974-06-14
BR4941/74A BR7404941D0 (en) 1973-06-20 1974-06-17 PROCESS FOR THE PRODUCTION OF NEW PYRIDAZINE COMBINATIONS AND PROCESS FOR SELECTIVE FIGHTING OF WEEDS
IT68890/74A IT1050518B (en) 1973-06-20 1974-06-17 PENYLPYRIDAZINIC DERIVATIVES, PARTICULARLY USEFUL AS DISINFESTANTS, AND PROCEDURE FOR THEIR PREPARATION
US05/480,309 US3953445A (en) 1973-06-20 1974-06-17 3-Phenyl-6-halo-pyridazinyl thio-and dithio-carbonates
LU70352A LU70352A1 (en) 1973-06-20 1974-06-18
AU70181/74A AU484628B2 (en) 1973-06-20 1974-06-18 Phenylpyridazines, their preparation and use as herbicides
DD179248A DD112205A1 (en) 1973-06-20 1974-06-18
BE145633A BE816574A (en) 1973-06-20 1974-06-19 PHENYLPYRIDAZINES AND PROCESS FOR THEIR PREPARATION
PL1974172058A PL100063B1 (en) 1973-06-20 1974-06-20 METHOD OF THE PRODUCTION OF NEW 3-PHENYL-4-HYDROXY-6-CHLOROCOPYRIDZYINE DERIVATIVES
JP6976774A JPS5420574B2 (en) 1973-06-20 1974-06-20
SU2037601A SU514569A3 (en) 1973-06-20 1974-06-20 The method of producing pyridazine derivatives
NL747408275A NL154213B (en) 1973-06-20 1974-06-20 PROCESS FOR THE PREPARATION OF A HERBICIDE PREPARATION BASED ON 6-HALOGEN-4-SUBSTITUATED-3-PHENYLPYRIDAZINE APPLYING THIS PROCEDURE OBTAINED FORMED HERBICIDE PREPARATIONS AND PREPARED PROCESS FOR THE PREVIOUSLY PREPARED APPLICATION.
PL1974193123A PL98549B1 (en) 1973-06-20 1974-06-20 WEDDING AGENT FOR SELECTIVE WEED CONTROL
SU2117535A SU526274A3 (en) 1973-06-20 1974-06-20 Method of weed control
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DE102008037629A1 (en) 2008-08-14 2010-02-18 Bayer Cropscience Ag Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides
WO2019018205A1 (en) 2017-07-18 2019-01-24 Christian Stratmann Herbicidal composition comprising mesotrione and pyridate and method of use thereof

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Cited By (1)

* Cited by examiner, † Cited by third party
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DE4013734A1 (en) * 1990-04-28 1991-10-31 Agrolinz Agrarchemikalien Muen Herbicidal compsns. contg. 3-phenyl-pyridazine derivs. - active against mono- and dicotyledonous weeds in e.g. cereal, onion, tomato or peanut crops

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AR205890A1 (en) 1976-06-15
IL45037A0 (en) 1974-09-10
DE2331398A1 (en) 1975-01-23
DD112205A1 (en) 1975-04-05
AT326409B (en) 1975-12-10
NL7408275A (en) 1974-12-24
AT326137B (en) 1975-11-25
PL98549B1 (en) 1978-05-31
ZA743763B (en) 1975-06-25
IT1050518B (en) 1981-03-10
BR7404941D0 (en) 1975-01-07
LU70352A1 (en) 1975-03-27
HU173167B (en) 1979-03-28
CH585013A5 (en) 1977-02-28
GB1441056A (en) 1976-06-30
CS172993B2 (en) 1977-01-28
DK137724C (en) 1978-10-02
IL45037A (en) 1977-03-31
DE2331398C3 (en) 1979-10-11
PL100063B1 (en) 1978-08-31
AU7018174A (en) 1975-12-18
DK137724B (en) 1978-04-24
YU39604B (en) 1985-03-20
ATA566173A (en) 1975-02-15
BE816574A (en) 1974-12-19
CA1013745A (en) 1977-07-12
KE2673A (en) 1976-12-10
YU155374A (en) 1982-06-30
DK312374A (en) 1975-02-10
ATA566273A (en) 1975-02-15
SU514569A3 (en) 1976-05-15
FR2234296A1 (en) 1975-01-17
NL154213B (en) 1977-08-15
US3953445A (en) 1976-04-27
JPS5420574B2 (en) 1979-07-24
JPS5035339A (en) 1975-04-04
SU526274A3 (en) 1976-08-25
FR2234296B1 (en) 1978-01-13

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